Best Vacation Rentals in Cheshire

Located in New Ashford, 19 miles from Cranwell Spa & Golf Club, The Springs Motel provides accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a terrace. Each room at the 4-star hotel has mountain views, and guests can enjoy access to a bar and to water sports facilities. The property has a concierge service and free WiFi. Complete with a private bathroom equipped with a shower and free toiletries, all guest rooms at the hotel have a flat-screen TV and air conditioning, and some rooms here will provide you with a balcony. The rooms will provide guests with a fridge. The Springs Motel has a grill. Tanglewood Musical Center is 19 miles from the accommodation, while Tanglewood is 19 miles away. Albany International Airport is 39 miles from the property.

- "Loved our stay, definitely would return" - "Memories were made that will last a lifetime and we definitely want to come back someday! Thank you!" - "Will definitely stay here again if we’re in the area." - "The loveliest motel I've ever stayed at" - "Perfect location!" - "Nice, retro place to stay. Close enough to Williamstown" - "Convenient." - "Cute, elevated motel" - "Loved it!" - "A lovely place but absence of management during the day."

Bed & breakfast in Cheshire with free breakfast
Coffee/tea in a common area, a library, and express check-in are available at this bed & breakfast. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, express check-out, wedding services, and a garden are onsite.
Housekeeping is not available.
Harbour House Inn offers 6 accommodations with bathrobes and hair dryers. Each accommodation is individually furnished and decorated. Satellite television is provided.

Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include complimentary toiletries and ceiling fans.

- "Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!" - "Lovely space and welcoming host." - "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "

Offering a tennis court, Mountain getaway in the Berkshires - walk to trails & town! offers accommodations in Adams. This vacation home features air-conditioned accommodations with a patio. There's an outdoor fireplace and guests can use free Wifi and free private parking. Featuring a terrace and mountain views, the spacious vacation home includes 4 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 2 bathrooms with a bath and a shower. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Guests at the vacation home will be able to enjoy activities in and around Adams, like skiing, cycling, and fishing. Outdoor play equipment is also available at Mountain getaway in the Berkshires - walk to trails & town!, while guests can also relax in the garden. Tanglewood is 23 miles from the accommodation, while Cranwell Spa & Golf Club is 24 miles from the property. The nearest airport is Albany International Airport, 48 miles from Mountain getaway in the Berkshires - walk to trails & town!.

Child Friendly • Other • Balcony/Terrace • View • Ocean View • Air Conditioner • Internet • Pet Friendly • Parking • Kitchen

While you're here, you can enjoy all the comforts of home and more, including a refrigerator and free WiFi, as well as an LCD TV and a coffee/tea maker. Other amenities include towels, slippers, a desk, and housekeeping.

- "The Revival House was charming and quiet. It had everything we needed for our short stay. It's only a 6 minute drive to the Bellows Pipe Trail/Mount Greylock, which was a huge plus for us. Wishing all the best for this newly opened hotel!" - "Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and " - "The inside is perfect. The neighborhood is unkept. A week of landscapers would make first impressions better. That being said the cover of the book is worn, the real treasure is the inside. I want this new hotel to succeed. It’s has an indescribable quality that makes this a must stay. "

The Trail in Adams - Berkshires' Art Hotel provides a hot tub and air-conditioned accommodations in Adams, 23 miles from Cranwell Spa & Golf Club. Among the various facilities are a garden, a terrace, and a shared lounge. The accommodation offers a sauna, free Wifi throughout the property, and family rooms. The bed and breakfast offers a flat-screen TV and a private bathroom with slippers, a hair dryer, and shower. At the bed and breakfast, all units are allergy-free. At the bed and breakfast, units come with bed linen and towels. The Trail in Adams - Berkshires' Art Hotel offers a vegetarian or gluten-free breakfast. For guests with children, the accommodation features an indoor play area. Skiing, cycling, and hiking are possible within the area, and The Trail in Adams - Berkshires' Art Hotel offers ski storage space. Tanglewood Musical Center is 23 miles from the bed and breakfast, while Tanglewood is 23 miles from the property. Albany International Airport is 48 miles away.

- "Charming bed and breakfast with friendly, accommodating owners." - "Excellent" - "Awesome vibes at The Trail in Adams!" - "Pleasant stay in updated small arts-oriented hotel in an up and coming small city." - "Will Return Again" - "Nice place to stay" - "I can’t wait to come back!" - "Pleasantly surprised!" - "Form over function"

With close access to the Ashuwillticook rail trail and a short drive to convenient shopping and restaurants, this is a perfect location for your Berkshire getaway. Relax on the private back porch, or in the large bath tub. Cook meals in the full kitchen, or do some writing at the desk with views of the pond. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer! 5 minute drive to Lakeview Orchards, 20-25 minutes from Lenox, Tanglewood, and Kripalu. 30 minutes to Mass MoCA and the peak of Mount Greylock (less to the start of the trails, if you want to hike it yourself!). 5 minute drive to Jiminy Peak, 45 to Berkshire East and Butternut ski resorts. 20 minutes to Notchview for cross country skiing.

This is a unique old house, and you will find nautical books and artifacts, as well as trinkets from around the world. Please note that there is no TV. The spiral staircase is one of my favorite features of the house, but it is narrow and steep, so please take care. If there will be more than two guests, and you require complete privacy from those staying on the couch downstairs, you might want to rethink, as the house is small and the bedroom upstairs is a loft. The bedroom upstairs has low ceilings - but with a comfy king sized bed, there's no need to stand up for too long, anyhow! In addition to the full bathroom downstairs, there is a half bath on the second floor, so one does not have to navigate the small staircase after bed time. The second bed, a pull out couch downstairs, is queen sized and very comfortable.

- "The cottage was clean and as described. The street was very quiet." - "This property is located near some great hiking, biking and swimming and is a great place to stay. If we had a question it was responded to in a very timely and professional manner. The owner made us feel more than welcome and went out of their way to make our stay exceptional. I would certainly stay here again!" - "We had a very enjoyable stay. The owner provided some basics such as coffee, tea and spices. The first level consists of the kitchen, living/dining room combo. There is a narrow spiral staircase to the bedroom which has access to a toilet and sink. We didn't stay up there as the pitched roof is too close to the bed and it was cold. The bathroom has a nice washer/dryer however the baseboard heater doesn't provide enough heat so it felt frigid. There is spa tub suitable for soaking but if you less agile you may have trouble getting into the tub. The living room couch opens to a double bed with linens in the storage part of the couch. There was good heat on the first level and the hot water heats up quickly. The house is situated close to Target and the Regal Berkshire movie theatre. It is 15-20 minutes to area attractions such as Edith Wharton's house, Ventford Mansion, Norman Rockwell Museum and Clark Art Institute, etc. We would stay here again."

Situated in Adams, 37 km from Tanglewood and 37 km from Cranwell Spa & Golf Club, Charming Adams Home Near Dtwn, Trails and More! offers air conditioning. This holiday home is 45 km from Norman Rockwell Museum and 19 km from The Clark Art Institute. With free WiFi, this 1-bedroom holiday home features a cable flat-screen TV and a kitchen with an oven and microwave. Towels and bed linen are offered in the holiday home. Tanglewood Musical Center is 37 km from the holiday home, while Bennington Battle Monument is 42 km from the property. The nearest airport is Albany International Airport, 77 km from Charming Adams Home Near Dtwn, Trails and More!.

Child Friendly • Parking • Wheelchair Accessible • Internet

Bed & breakfast with free parking, steps from Adams Theater
This smoke-free bed & breakfast features coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area. Free WiFi in public areas and free self parking are also provided. Other amenities include an arcade/game room, express check-in, and a garden.
The Trail in Adams - Berkshires’ Art Hotel offers 9 air-conditioned accommodations with slippers and hair dryers. These individually decorated and furnished accommodations include desks. Beds feature premium bedding. Televisions come with digital channels, pay movies, and Netflix. Guests can surf the web using the complimentary wireless Internet access. A nightly turndown service is provided and housekeeping is offered daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Went to Solid Sound music fest in North Adams and needed a place to stay. The Trail was available and we were pleasantly surprised!" - "nice comfortable and funky!" - "We loved this place, it was fun, quirky and cute. It felt like being at home, honestly. I have an injury and the staff was able to accommodate an earlier check-in without any issue. The staff was very kind and responsive. My fiancé loved the shower sauna! Awesome place to stay!"

Lakeside Berkshires Home Near Hiking and Skiing! is located in Lanesborough, just 12 miles from Tanglewood Musical Center and 13 miles from Tanglewood. This vacation home features accommodations with a balcony. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Norman Rockwell Museum is 18 miles from Lakeside Berkshires Home Near Hiking and Skiing!. Albany International Airport is 43 miles from the property.

Guest Services • Security/Safety • Spa • Other • Child Friendly • Accessibility • Internet • Parking

Motel in New Ashford with free parking
This motel features a seasonal outdoor pool, a garden, and charcoal grills. Free WiFi in public areas and free self parking are also provided. Other amenities include a picnic area and a banquet hall.
Housekeeping is available on request.
The Springs Motel offers 20 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and complimentary toiletries. Each accommodation is individually furnished and decorated. Smart televisions are featured in guestrooms.

Bathrooms include shower/tub combinations. This New Ashford motel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Housekeeping is provided on request.

- "Great motel! Clean, well-decorated, decent-sized rooms and a lovely grassy courtyard with comfy furniture, picnic tables, umbrellas, and fire pits. Although right off the highway, the road noise was minimal and it was a very relaxing place to crash for a night. " - "We really enjoyed the wonderfully updated Atomic ranch style. It had all the 50’s charm With a nicely updated, modern feel. Rooms were well appointed, clean and great to stay in. Mattress and pillows were comfy and we thoroughly enjoyed our stay."

This Lanesboro, Massachusetts motel is located less than 1 mile from Pontoosuc Lake and features free Wi-Fi access and cable TV in every room. Balance Rock State Park is 2 miles away. The Weathervane Motel Lanesboro features rooms with a microwave and a refrigerator. They also offer coffee making facilities and an private bathroom with a hairdryer. Guests can relax in air conditioned comfort at the Lanesboro Weathervane Motel. A garden and vending machines with drinks are also available. The Berkshire Museum is 10 minutes’ drive from the motel. The Bousquet Ski Area is 7.8 mi away, while the Jimmy Peak Ski Area is 8.2 mi away.

View • Other • Skiing • Internet • Guest Services • Air Conditioner • Child Friendly • Parking • Fireplace/Heating

Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, extra linens and blankets. Nice front and back porches.

Plenty of parking. Centrally located in the beautiful Berkshires, a short drive to anything. The stairs are very quirky and not for the faint at heart. You'll love them or hate them! See picture.

***NOTE: We are family-friendly! We make an extra effort to ensure that children and pets feel welcome and are comfortable. No breed or size limits for dogs!

180-year-old home with plenty of modern updates to make anyone feel at home.

2 bedrooms , one with a king bed and the other with a trundle with 2 twin beds. There is a Queen air mattress, able to be set up in any room guests choose. Pack and Play with sheets and blankets is also always available and can be used in any room. Extra sheets, blankets, and pillows are always available.

There is other equipment for traveling babies and toddlers, such as an infant swing, boppy, Bumbo seat, wagon, and toys. A stroller can be provided with advance notice.

The modern bathroom features a large walk-in shower and a hair dryer for convenience.

WiFi and smart TVs make your downtime relaxing. Alexa in the kitchen can be moved to any room you choose.

Modern washer and dryer is available for use at any time at no charge.

Experience what the Berkshires has to offer in this centrally located home in the friendly and safe town of Dalton! While visiting, don't forget to stop at Waconah Falls, The Pines, and Holiday Brook Farm!

- "The property was very clean, easy to access and amazing with all the extras that most places don’t include. The water was really hot and it never ran out. The bed was out of this world comfortable. Property owner was very responsive and more than willing to help. Dogs welcome. I would definitely recommend this property. I hope to return sometime in the near future " - "This is an incredibly well renovated and extraordinarily comfortable house - one might never guess given the age of the property! It has been very tastefully decorated, and the thoughtfulness of the owner/operator is eminently evident. With the many (over 15) wonderful experiences I have had in recent year at VRBOs this one still stands out due to the extremely well stocked nature of the house in general, and the kitchen in particular! Additionally we were permitted to park a car in the abundantly large parking space outside of our reservation hours which made a HUGE difference in the convenience afforded to our point to point hiking the Appalachian Trail in the Cheshires. All of us who stayed would wholeheartedly recommend this as THE place to stay if hiking the Appalachian Trail in Massachusetts or theCheshires! "

Harbour House Inn B&B enjoys a location in Cheshire, 20 miles from Tanglewood and 25 miles from Norman Rockwell Museum. 19 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center, the property offers ski storage space and a garden. The bed and breakfast provides rooms with air conditioning, free private parking, and free Wifi. At the bed and breakfast, all units have a wardrobe and a flat-screen TV. There's a private bathroom with bath in some units, along with bathrobes, a hair dryer, and free toiletries. At the bed and breakfast, every unit has bed linen and towels. Guests at the bed and breakfast will be able to enjoy activities in and around Cheshire, like fishing and hiking. Guests at Harbour House Inn B&B can enjoy skiing and cycling nearby, or make the most of the sun terrace. Bennington Battle Monument is 29 miles from the accommodation, while The Clark Art Institute is 15 miles away. Albany International Airport is 47 miles from the property.

- "This was the nicest inn we’ve ever stayed in; so charming and clean and the host was wonderful-we will definitely stay h" - "Great choice for “Inn to Inn” hiking on the AT." - "A perfect getaway. A lot to do in the Berkshires."

Bright and spacious, 25 ft ceiling, Post & Beam home on 25 private, hillside acres, nestled in the middle of the Berkshires, minutes from Lenox, Tanglewood, Williamstown, Pittsfield, Mount Greylock, Rail to Trails, Balance Rock State forest, the Appalachian Trail, skiing in Massachusetts (Jiminy Peak, Bosquet, Butternut) and Vermont (Bromley, Stratton), antiquing, orchards, and amazing BBQ at Biggin’s Diggins. 10 minutes to swimming and boating in Lake Pontoosuc, 8 minutes to skiing at Jiminy Peak and ropes adventures at Ramblewild. With 4 bedrooms (including a Bunk Room), the house can sleep 10 people in beds, and 12 including a pullout queen sofa bed.

Description:

As you drive up the long windy driveway of this private, secluded 25 acre property, you feel enveloped by the forest. When you near the top of the hill, the forest opens up to a contemporary mountain home. As you walk into the house thru the mud room, the Great Room opens before you with a soaring, 25ft ceiling, sunlight streaming in thru windows, skylights and sliders everywhere, and the rich smell of yellow pine. The entire house is walled with tongue-in-groove yellow pine, with giant wood beams that run the length of the house and equally large cross beams and exposed joists, making a lattice of wood from floor to ceiling. Comfortably furnished and well appointed with all the comforts of home, you have multiple ways and places to relax. You can flop down on the giant sectional and put your feet up, go upstairs to the balcony and stretch out with a book or a game, go down to the lower level lounge and watch a movie on the 65” Samsung TV, retreat to your bedroom and take a nap curled up with feather and down pillows, or sit on the deck and bird watch at one of the feeders.

Main Floor
The entire main floor is an open floor plan, with windows of all shapes and sizes, pine plank floors, and 4 sliders leading out to different parts of the huge deck. With the kitchen, living and dining areas open to each other, it lends perfectly to socializing and spending time with a group, whether you are on a multi-family holiday, a friends reunion or a single-family getaway. A fully appointed kitchen, with new high-end stainless steel appliances (GE Café 6-burner gas range/oven, Café Refrigerator, and a Bosch dishwasher), granite countertops, All Clad and Cuisinart cookware, Henkel cutlery, bakeware, serving platters, bowls and more, is ideal for making gourmet spreads to simple meals alike. People can eat at the large farm table (which can comfortably fit 10 or, with the extension, 12) in the dining area, on the screened in porch, or pull up a stool and sit at the eight foot island, perfect for socializing and helping with the meal prep. A big sectional faces a fully functional wood burning stove keeping you warm during those cold winter nights. And, for the more competitive types, there is a full-size foosball table with plenty of space around for spectators.

Second Floor
As you walk up the wide stairs, you pass by an enormous angular plate glass window giving you a view out front and (in Spring) the Robin’s nest with babies, that sit on the outside sill. At the top of the stairs is an upstairs loft area with a small sectional couch that turns into a queen size sofa bed. You can watch the large 65” Samsung TV or pick a book or puzzle to relax. Along the railing you get a full view of the main floor layout just before you enter the master/primary bedroom. As you walk in, you see the giant beams and a cathedral ceiling, a king size bed, a long bench under a wall of windows facing south west, and an en suite bathroom with a double sink vanity.

Lower level
As you walk downstairs from the main level, you move from soaring timbers to a cozy lounge. The lower level lounge has a large sectional that can seat 6 in front of the large screen tv, or play board games on the large coffee table. As you work your way back you find 2 queen bedrooms, one with a built-in bed, and the other an impressive sleigh bed. Walking down the short hall you pass the other full bath and head into the bunk room, with handmade, sturdy, built in bunk beds and plenty of drawers for clothing.

Amenities:
Every convenience of living at home is provided whether it is choosing from any variety of puzzles and boardgames, cotton sheets (flannel for winter!), new mattresses and feather pillows (hypo-allergenic too!), to Smart TV’s, high speed WiFi, Alexa for music, cable and streaming services (or use your own), soap/shampoo, hair dryers, iron/ironing board, towels, washer/dryer, dishwasher, Braun coffee brewer, Keurig coffee maker, toaster oven, food processor, pots, pans, blender, baking and serving dishes, knives and utensils. Basic spices and baking ingredients are available, as well as condiments (tho many prefer to buy their own). You need only bring or toiletries and any food!

Property
This striking contemporary house sits on 25 acres of very private woodland property, situated on the backside of Jiminy Peak, the largest ski mountain in Massachusetts. We abut 500 acres of private property and sit up the hill a couple hundred feet from the road, which makes it an exceptionally peaceful and quiet location. You are truly in nature. The sights and sounds of the forest are with you day and night, from the wind rustling the leaves and deer walking across the yard to the family of owls swooping from tree to tree and coyotes calling at night. We recently took down some trees to open up the space around the house, and create future space for more lawn and plantings, with the huge trees resting on the forest floor. The woods are lovely, looking densely packed from a distance but as you walk, you realize there is plenty of open space around you.

Location and Things to Do
Sadie’s Woods is the ideal location for the outdoor enthusiast, as well as those who enjoy cultural pursuits.
In winter: For skiing, we are less than 10 minutes from Jiminy Peak, and 45 mins or less to 4 other family ski mountains. For the more adventurous skiers, we are an ideal jumping off point for day trips to VT resorts Bromley and Mount Snow, a little more than an hour away.
In Spring, Summer and Fall: We are a 5 minute drive from Pittsfield state forest and Balance Rock State Park, and 15 mins to Appalachian Trail access, with lots of great hiking within minutes of the house. For bikers and walkers, it is only 6 minutes to the beginning of Ashuwillticook Rail Trail, one of the longest in MA. For fishing, water sports and swimming, Lake Pontoosuc is 10 mins away, and Cheshire reservoir is 15 mins. There are 3 golf courses within 10 miles.
The location is also perfect for those who want to enjoy culture and history from all parts of the Berkshires, from the Mass MoCA museum, Hancock Shaker Village and the Clark Art Institute, to music at Tanglewood or theater in Williamstown, being equidistant to both. On the way you go thru historic towns like Pittsfield, Lenox, and Adams (each with their own attractions). In each of these charming New England towns are fantastic food options for every meal.

- "We enjoyed this beautiful home for a break last week! From the minute we pulled off the main road we knew we were in for a special few days. The great room has large windows providing lots of sunlight and a panoramic view of the surrounding woods. The elevated deck was the perfect spot to enjoy my morning coffee and book-it was like being in a treehouse. The house is a quick drive to Tanglewood, the reason for our visit. The hosts, Kim and Chip have thought of everything: the house has tons of amenities, a full gourmet kitchen, huge sectional sofa and even a foosball table! It would be an ideal winter revisit for ski season (wood burning stove and that kitchen) or leaf peeping- with plenty of space to return with friends! "

Located in Adams, within 23 miles of Cranwell Spa & Golf Club and 23 miles of Tanglewood Musical Center, The Revival House provides accommodations with a shared lounge and free WiFi throughout the property as well as free private parking for guests who drive. The property is around 23 miles from Tanglewood, 25 miles from Bennington Battle Monument and 28 miles from Norman Rockwell Museum. The hotel features family rooms. The private bathroom is equipped with a shower, a hairdryer and slippers. Guest rooms at the hotel include air conditioning and a desk. You can play table tennis at The Revival House. The Clark Art Institute is 12 miles from the accommodation, while Southern Vermont College is 24 miles away. Albany International Airport is 48 miles from the property.

- "Interesting overnight stay in old home in the Berkshires" - "We enjoyed it and would like to go back again." - "We enjoyed our stay"

Private, unique getaway in the center of the Berkshires. We're a 3 minute walk to the Ashuwillticock rail trail. Situated on over 100 wooded acres with lots of walking trails, extraordinary trees, land forms and private seating areas and spaces to explore.

The cottage is a newly built. Super comfortable space above a stand alone 3 car garage. We have a private entry driveway and parking area exclusive to the cottage. Open floor plan with fun window seats, full kitchen and living room and full bath. It's a unique thoughtful design.

Radiant floor heat in the winter, central A.C. in the summer.

- "Great location, property and host. Very clean space. Lots to do around with great food options. Definitely coming back." - "From check-in to departure, this sweet, attractively appointed, large studio space, on beautiful grounds, in a great location was the perfect home base for an outstanding long weekend in the Berks. Would return in a heartbeat." - "We had a wonderful weekend at the Carriage House. The photos show the nice secluded location, but it is only a few turns from shopping centers, grocery stores, and downtown Pittsfield. The nearby rail trail is newly paved and a beautiful walk through the woods. The apartment has all necessities for a great getaway in the Berkshires!"

If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a guest house - since 1998.

PLEASE NOTE: It's an old building with an unusual layout, so please carefully read the description below.

Beautifully situated amidst horse farms on the scenic road to Mt Greylock. In the center of the Berkshires, 5 miles from Jiminy Peak ski area, 10 miles from South Williamstown, 15 miles from Tanglewood and Mass MoCA, and 20 miles from Jacob's Pillow. 5 miles to Pittsfield and the Berkshire Mall. Private garden. 5 acres of property in the back where horses graze, and alpacas, donkeys and other friendly animals next door.

Everything is provided: fully-furnished mostly with antiques. Bedspreads, linens, blankets, pillows, towels, iron and ironing board. SMALL KITCHEN with mini stove/oven, refrigerator, microwave, Keurig coffeemaker with assortment of coffee, tea and hot chocolate, pots and pans, dishes, cutlery, etc. Broadband internet and TV with Netflix, Hulu and other streaming options included.

There are 2 floors. The first floor is the old classroom with old desks. There is also a trundle bed which can be used as 2 twins. The bathroom is on the first floor. The 2nd floor is like a studio apartment - with a queen bed and a twin bed and the small kitchen. PLEASE NOTE: There is one bathroom, on first floor.

Ideal for a romantic getaway or for a family of 4-5. A fee of $25/night applies for additional adults after the first two (limit of 4 adults total). No extra charge for children. Please indicate the number of children in your message to us, but select 0 children in the pull-down menu so that you are not charged.

The Old Stone School is available to rent 12 months a year. Each season has it's benefits:

SPRING - Trees arise from winter sporing their fleeting Spring green color, daffodils, tulips, hiking trails are open, enjoy the warm weather after a long winter! Calves appear on the hill behind the schoolhouse.

SUMMER - Flowers blooming, berries to pick, outdoor activities nearby, culture everywhere - Tanglewood, Jacob's Pillow, Barrington Stage, Clark Art Museum, MassMoCA, Williams College Museum of Art, etc.

FALL - Enjoy the kaleidoscope of Fall colors covering the hills behind the schoolhouse. Hike Mt. Greylock - short and long hikes. Go the top and check out Bascom Lodge - a stop on the Appalachian Trail.

WINTER - Jiminy Peak is less than 10 mins. away.Ski or snow tube at Bousquet is 20 mins. away. Cross country Ski in the fields out back or go to Hilltop Orchards in Richmond or Notchview in Windsor.

- "Our stay at this historic schoolhouse was terrific. The owner was very welcoming and helpful. We slept well there - as the two available large rooms up and down afforded flexible sleep areas. Beds comfy. The kitchen was well equipped and the amenities such as foil, plastic wrap, tea, a Keurig machine, extra paper plates etc made our stay very convenient. The history of the place is fascinating. Many thanks!" - "This charming converted schoolhouse is well-supplied for the present day while reminding you of a bygone age. It's set among beautiful rural woods and pastures, private, but with ideal access to local attractions south, like Stockbridge and Lenox or north, like Williamstown and North Adams. The owners are extremely helpful and friendly, and they also simply allow you to enjoy your stay. A great place!"

Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroom ranch is located in the quaint town of Adams at the base of Mt. Greylock. You can enjoy the many outdoor activities year round right out the back door. Play a round of gold at a nearby golf course, Hiking trails only steps away, MTB trails and the Ashuwillticook Rail Trail all within a mile, as well as many back roads to explore on your road bike. Snowshoe or ski Mt. Greylock in the winter months and leaf peep and hike during the Fall. Visit a museum or see a dance troupe or play at one of the many Theaters in the area. Enjoy local musicians in one of the many local parks that host Music in the Park or catch a concert at Tanglewood or MassMoca or the Newly opened Adams Theater. There are many museums in the area for young and old along with summer fun in town and in the surrounding towns. Bring the little ones and enjoy a picnic on top of Mt. Greylock, a swim at Windsor Lake or a little splash time at the free splash pad just 5 minutes away.

PET FEE: Please indicate if you are traveling with your pet(s). There is an additional set rate pet fee charge of $100.00 to cover the the additional cleaning costs.

Please indicate the number and type/size of pets upon booking, maximum pets allowed is 2, additional fee for more upon approval.

Let’s keep the Greylock Getaway pet friendly. I know I loved being able to travel with my pet, and I appreciate people who allowed me to bring him along and I understand the extra costs that come along with it, but he was worth it. I’m sure yours are too. Neighborhood and trails at the Greylock Glen are very pet friendly.

10 min drive to Windsor Lake in North Adams to enjoy fishing, swimming and Kayaking and 10 minutes South to Cheshire lake for kayaking and fishing. Enjoy Tanglewood, MassMoca, Clark Art, or one of the many other museums or theaters in the area as well. You will never be short on things to do in the Berkshires.

A 5 min drive to North Adams, 10 min to Cheshire, 15 to Williamstown, 20 min to Pittsfield, 40 min to Tanglewood, 35 min to Jiminey Peak Ski Area.

Check us out on Facebook TheGreylockGetaway to see what is happening in town and around the area.

*Please be aware this home has stairs, the front deck has 4 steps, back deck has 3 steps, same level access from lower level driveway or one full flight of stairs to main level living space from lower level family room (futon sleeping area), second bathroom/laundry room and extra bonus room on lower level.

* During the summer months, lawn care is done weekly. If you are staying for a full week this may fall on one of the days you will be there. You will get notice of that day. Snow removal is done as needed. Extra shovels and salt are provided for your use.

*Trash removal is done on Wednesday, Thursday or Saturday as needed. If it falls on a day you are occupying the home you will be notified ahead of time that I will be stopping by for a trash pickup.

** I No longer accept monthly long term rentals, maximum stay 2 -3 weeks unless approved for a longer stay.

***This home is protected by a WYZE security camera outside the home in driveways only.

- "Julie was very attentive in communicating with us and providing details of the home and surrounding area. Close to Mass MOCA and Clark Art Institute (short drive), sweet clean home. I came with a friend but had a nice selection of toys/games for young kids and a fenced in yard with a play area/jungle gym." - "We had a fantastic stay in Adams for a family reunion. This house was perfectly located right by Mount Greylock trailheads and Pecks Falls. Our Great Grandmother used to live in a house down the street so this was a wonderful trip down memory lane for us! Julie was so helpful and kindly left extra dog towels and bowls out! The fenced in backyard was super convenient and we loved all of the patio furniture!"

Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen, new bathroom with tub/shower. Washer, dryer, electric fireplace, deck, and hot tub. Fire pit, horseshoes, walking trails, use of field, and access to adjacent garden center full of colorful shrubs and perennials.

- "It was nice even in the rain." - "The listing doesn't do justice to this place. The house is cozy, well maintained and clean, everything works. The location is great and there is a huge backyard to explore. Communication with Susan was great and she was very responsive and nice, like a true friend. We assisted to a wedding nearby and we took advantage to stay a few more days and having a great time. A beautiful place and a great house to come back...Truly recommended."

2 MIN TO JIMINY PEAK - right down the road and next door to RAMBLEWILD-
#1 AERIAL ADVENTURE PARK IN THE BERKSHIRES! Close to Lenox and Williamstown! Reduced rates. Great for 2 families (max 8 persons!) Come and enjoy our beautiful mountain retreat - A home for every season. This charming and secluded home away from home is a wonderful place for family, friends and romance. Only 2 minutes from Jiminy Peak, 15 min to Williamstown and 25 minutes to Lenox!! Book now!!! House comfortably fits 2 families with small children- see reviews

With over 2200 square feet, this beautiful secluded house with beautiful mountain views has plenty of space for everyone yet a very cozy feel. Each one of the 3 large bedrooms has walk-in closets and beautiful wood furnishings. The master suite has a king size bed and matching furniture with a 50” Samsung LCD HDTV. The attached master bathroom has a huge Jacuzzi tub for two. Step out onto the balcony from the living room for a magnificent open view of the mountains. Enjoy a movie on your 65” Samsung smart HDTV while enjoying the heat from the wood-burning stove. The enclosed basement can be used as a playroom or den with a bar and bar stools, an office with a desk and new HP printer, or as a closed-off 4th bedroom with a couch that opens up into a queen sized bed. Another Samsung 50” Smart TV is there. Explore the 16 acres of trails on the property and hike your way to the golf course in the back. If you have kids, there are swings and slides on the property for their enjoyment. There's also an attached 2 car garage so that you can come directly into the warm house after a long day of skiing.

There is also a fully stocked kitchen with all new appliances (bought in 2024) and a dining room which seats 8 persons. The laundry room also has a new washer and dryer.

And don't forget that just 2 miles down the road is Jiminy Peak - offering skiing and snowboarding day and night in the winter and mountain coaster and rides in summer. We are located about 25 minutes from Tanglewood. Or drive ten minutes down the road to the Clark Museum in Williamstown and enjoy some Monet and Renoir. Or fifteen minutes down the other direction to the city of Pittsfield for some wonderful restaurants and shops- as well as a beautiful lake for boating and swimming. And don't forget that we are only 2.5 hrs from NYC.

House is disinfected and sanitized after every guest by housekeeper who wears mask and gloves. No Contact check-in and check-out.

Keywords: House, Jiminy Peak, Berkshires, ski, hike, Lenox, Williamstown, Pittsfield, Hancock, Mountain, secluded, Lanesboro

- "Great experience. Deborah was great to deal with. The house was everything it was described? Definitely go back again!" - "We highly recommend this house. The accommodations and the many amenities helped make our family’s stay comfortable and enjoyable. The house is centrally located between Pittsfield, MA and Williamstown, MA. This made it convenient for our family to attend our daughter’s commencement activities at Williams College, plus expanded our choices in shopping & restaurants. Also, the host was very responsive to our questions prior to our arrival. Thanks for your hospitality Debbie :-) The ONLY recommendation for improvement would be to better post the address sign on the driveway’s entrance to the property. The sign was propped up on the ground which makes it difficult to see, especially at night."